I just finished the sweetest weekend trip. I left on Saturday morning and took Old San Pedro Mountain Road on my way to the Pigeon Point Lighthouse at the end of the first day. The next day I cruised into Santa Cruz after a stop in Ano Nuevo and Davenport. My ride was only about 50% on the coast highway, the other half I spent on the old stage road a few miles inland. This is a great tour if you only have a weekend and is easily expandable south or east. After I got to Santa Cruz I took the express 17 bus to San Jose where I caught the Caltrain back to SF. You can find more info about my trip here:
Send me a message, I am happy to answer any questions you might have.